Sodium Carbonate → HCID 58456380、化合物

HRID 410439ノート

反応式

HRID 410439 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(O)(/C=C/B1O[C:23](C)([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]1)C>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6](/[CH:25]=[CH:23]/[C:22]([CH3:28])([OH:21])[CH3:27])[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 11117347(E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol

生成物 1

HCID 58456380HCID 58456380、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2,4-dichloropyrimidine (71 mg, 0.476 mmol) in dioxane (4 mL) and sodium carbonate (2M in water, 0.25 mL, 0.5 mmol) were added (3E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol (100 mg, 0.476 mmol) and tetrakis triphenylphosphine palladium(0) (55 mg, 0.048 mmol). The solution was degassed by bubbling nitrogen gas and heated to 90° C. for 2 hr. The solution was diluted with EtOAc, washed with brine, dried with MgSO4, filtered, and concentrated to dryness. The residue was purified by flash chromatography on silica gel (0-100% EtOAc/hexanes) to afford (3E)-4-(2-chloropyrimidin-4-yl)-2-methylbut-3-en-2-ol as a colorless oil. MS ESI: [M+H]+ m/z 199.1. 1H NMR (500 MHz, CDCl3) δ 8.52 (d, J=5.1, 1H) 7.24 (d, J=15.6, 1H) 7.12 (d, J=5.1, 1H) 6.60 (d, J=15.6, 1H); 1.22 (s, 6H).

後処理

  1. customThe solution was degassed
  2. customby bubbling nitrogen gas
  3. additionThe solution was diluted with EtOAc
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash chromatography on silica gel (0-100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b8245dda30574070a2d40f02df856aac
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

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